Some communication applications such as email applications may provide rich attachment capabilities, where physical or cloud-based attachments can be sent/displayed along with metadata that may be live. When an email is sent from a communication service with rich attachment capabilities to another communication service without rich attachment capabilities that cannot handle the rich attachment features, the attachment may be brought into the email body as an HTML link. When the same message is subsequently sent to an account at the rich attachment capable communication service from the other communication service without rich attachment capabilities, the attachment is typically presented still in HTML link form unable to take advantage of the rich attachment capabilities of original communication service.